gamma-silyloxy-benzyllithiums: Stereochemistry of the retro-[1,4]-Brook rearrangement

被引：12

作者：

Bousbaa, J ^{[1
]}

Ooms, F ^{[1
]}

Krief, A ^{[1
]}

机构：

[1] FAC UNIV NOTRE DAME PAIX,DEPT CHEM,LAB CHIM ORGAN SYNTHESE,B-5000 NAMUR,BELGIUM

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 43期

关键词：

D O I：

10.1016/S0040-4039(97)01810-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Although gamma-sulfonyloxy-benzylselenides react with butyllithium to produce stereospecifically aryl cyclopropanes, the corresponding gamma-silyloxy-benzylselenides lead to a stereoisomeric mixture of gamma-hydroxy-alpha-silyl-benzylselenides via the retro-[1,4]-Brook rearrangement. Apparently the intermediate benzyllithiums are alkylated before epimerisation takes place in the first case, whereas in the second one epimerisation occurs prior to the silyl group migration. (C) 1997 Elsevier Science Ltd.

引用

页码：7625 / 7628

页数：4

共 37 条

[1] AHLBRECHT H, 1995, LIEBIGS ANN, P211
[2] BEHRENS K, 1995, LIEBIGS ANN, P385
[3] ALPHA-OXYGEN-SUBSTITUTED ORGANOLITHIUM COMPOUNDS AND THEIR CARBENOID NATURE - CALCULATIONS OF THE CONFIGURATIONAL STABILITY AND OF LICH2OH MODEL STRUCTURES, CRYSTAL-STRUCTURE OF DIPHENYL(TRIMETHYLSILYLOXY)METHYLLITHIUM.3 THF, AND THE STEREOCHEMISTRY OF THE (REVERSE) BROOK REARRANGEMENT
BOCHE, G
OPEL, A
MARSCH, M
HARMS, K
HALLER, F
LOHRENZ, JCW
THUMMLER, C
KOCH, W
[J]. CHEMISCHE BERICHTE-RECUEIL, 1992, 125 (10): : 2265 - 2273
[4] SOME MOLECULAR-REARRANGEMENTS OF ORGANOSILICON COMPOUNDS
BROOK, AG
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 1974, 7 (03) : 77 - 84
[5] BRUCKNER R, 1994, SYNLETT, P1049
[6] THE 1, 4 O-]C SILYL MIGRATIONS OF VARIOUS 3-[(TRIALKYLSILYL)-OXYMETHYL]-FURANS AND 3-[(TRIALKYLSILYL)-OXYMETHYL]-THIOPHENES
BURES, EJ
KEAY, BA
[J]. TETRAHEDRON LETTERS, 1987, 28 (48) : 5965 - 5968
[7] ENANTIOSELECTIVE SYNTHESIS OF GAMMA-HYDROXYSILANES, 1,3-DIOLS AND CYCLOPROPANES BY REACTION OF A CHIRAL EPOXIDE WITH A RACEMIC ALPHA-SILYL ORGANOLITHIUM REAGENT
COREY, EJ
CHEN, ZL
[J]. TETRAHEDRON LETTERS, 1994, 35 (47) : 8731 - 8734
[8] ORGANO-SILICON COMPOUNDS WITH FUNCTIONAL-GROUPS PROXIMATE TO SILICON .15. 1,N-TRIORGANOSILYL MIGRATIONS IN THE REARRANGEMENTS OF SILYL-SUBSTITUTED ORGANO-LITHIUM COMPOUNDS
EISCH, JJ
TSAI, MR
[J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1982, 225 (01) : 5 - 23
[9] ELIEL E, 1990, ISR J CHEM
[10] PHOSPHONAMIDE STABILIZED ALLYLIC CARBANIONS - NEW HOMOENOLATE ANION EQUIVALENTS
EVANS, DA
TAKACS, JM
HURST, KM
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1979, 101 (02) : 371 - 378

← 1 2 3 4 →